Oakstead is a family-friendly Community Development District, also known as a CDD. The land Oakstead sits on was originally owned by the family of Milo Thomas and Fred Jones. Devco IV, L.L.C. purchased 878 acres in the year 2000 and named the property Oakstead. Oakstead is a gated community comprised of 9 subdivisions with 1184 homes. The first subdivision to be developed was Brenford, followed by Keswick, Strathmore, Ashmonte, Weymouth, Hillington, Ballastone, Marchmont and Tanglewylde respectively. Tanglewylde and Weymouth are maintenance free villas while the rest of the communities are single family homes. Oakstead residents share approximately 45 beautifully manicured acres of common area including 65 ponds, a 2-mile nature path and a community clubhouse with pool, tennis courts, basketball courts, and a fitness center. Oakstead is located within 25 minutes from the Tampa International Airport and 15 minutes from the Wiregrass Mall. Oakstead Elementary School is located right in Oakstead and the high schools are within a mile from the community.
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